EP0171112A1 - Diglyceride enthaltendes Fett - Google Patents

Diglyceride enthaltendes Fett Download PDF

Info

Publication number
EP0171112A1
EP0171112A1 EP85201190A EP85201190A EP0171112A1 EP 0171112 A1 EP0171112 A1 EP 0171112A1 EP 85201190 A EP85201190 A EP 85201190A EP 85201190 A EP85201190 A EP 85201190A EP 0171112 A1 EP0171112 A1 EP 0171112A1
Authority
EP
European Patent Office
Prior art keywords
diglycerides
fat composition
composition according
edible fat
acid residues
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85201190A
Other languages
English (en)
French (fr)
Other versions
EP0171112B1 (de
Inventor
Janos Bodor
Jan Van Heteren
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever PLC, Unilever NV filed Critical Unilever PLC
Priority to AT85201190T priority Critical patent/ATE31599T1/de
Publication of EP0171112A1 publication Critical patent/EP0171112A1/de
Application granted granted Critical
Publication of EP0171112B1 publication Critical patent/EP0171112B1/de
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01Other fatty acid esters, e.g. phosphatides
    • A23D7/013Spread compositions

Definitions

  • the present invention relates to edible fat compositions containing one or more diglycerides or a mixture of one or more diglycerides and one or more monoglycerides and to butter-like water- and oil-containing emulsions wherein the fatty phase contains said fat composition.
  • Products having butter-like properties have an elasticity, a plasticity and a melting behaviour comparable to those of natural butter.
  • the invention is based on the discovery that specific diglycerides have a profound influence on the crystallization behaviour of fats.
  • the edible fat composition according to the invention comprises one or more diglycerides or a mixture of one or more diglycerides and one or more monoglycerides, wherein:
  • the diglycerides or the mixture of diglycerides and monoglycerides crystallize within a temperature range similar to that of the fat composition in which they are incorporated. If the diglycerides or the mixture of di- and monoglycerides are liquid within a temperature range varying from the refrigerator temperature (about 5°C) to the ambient temperature (25 - 30°C), their influence on the fat is very limited. If, however, the melting point of the diglycerides or the mixture of mono- and diglycerides is too high, this will have a detrimental effect on the organoleptic properties (melting behaviour) of the fat composition and the emulsions prepared therefrom.
  • the diglycerides or the mixture of di-and monoglycerides in the fat composition melt between 20 and 40°C and preferably between 25°C and 40°C. This is mainly influenced by the level of C 16-22 fatty acid residues, as stated above. The preferred level of these residues ranges from 5 to 35 wt.%, based on the total weight of the fatty acid residues of the diglycerides.
  • C 12 - and C 14 - saturated fatty acid residues will range from 0 to 35 wt.% and preferably should be as low as possible, particularly between 0 and 15 wt.%.
  • the level of mono-cis and di-cis unsaturated fatty acid residues with a chain length of 18 or more carbon atoms in the diglycerides will generally not exceed 70 wt.% and preferably ranges from 25 to 65 wt.%.
  • the level of mono-trans unsaturated fatty acid residues with a chain length of 18 or more carbon atoms can be 0% but should not exceed 70% and preferably ranges from 5 to 60 wt.%.
  • the preferred diglycerides are for the purpose of this invention selected from the group consisting of diglycerides from 1 palmitic acid or stearic acid residue and 1 oleic acid residue, diglycerides from 2 elaidic acid residues and diglycerides from 1 elaidic acid- and oleic acid residue.
  • Amounts of diglycerides which are suitable for imparting butter-like properties preferably range from 10 to 20 wt.% based on the total fat composition and ideally on the amount of fat in the composition which is crystallizable within the temperature range of 5-35"C.
  • the diglycerides can be introduced in the fat composition as pure chemical compounds or as mixtures with saturated and unsaturated monoglycerides.
  • Monoglycerides seem to have a negative effect on the performance of the diglycerides. Saturated monoglycerides have a more negative effect than the unsaturated monoglycerides.
  • the ratio of diglycerides to saturated monoglycerides preferably exceeds 10 : 1 and the ratio of diglycerides to unsaturated monoglycerides preferably exceeds 6 : 1.
  • the diglycerides or the mixture of mono- and diglycerides useful for the purpose of the present invention may consist of the residual product from the distillation of monoglycerides which has optionally been subjected to further fractionation to isolate purified diglycerides.
  • the diglycerides of the fat compositions according to the invention preferably consist of a mixture of diglycerides obtained by interesterification of a fat or of a fat component of the fat composition, in the presence of an alkali- hydroxide and an amount of glycerol which may range from 0.5- 3 wt.% (based on the weight of the fat subjected to glycerolysis) and a conventional interesterification catalyst such as an alkaliglycerolate or an alkaliethanolate.
  • Excess monoglyceride formed during interesterification can be removed by physical methods such as chromatography or by chemical methods e.g. by treating the mixture with an alkali under conditions leading to hydrolysis of the monoglyceride and subsequently removing the soap produced therefrom.
  • oils and fats used to produce the edible fat compositions according to the invention can be of animal or vegetable origin and may include, for instance, palm oil, lauric fats, soybean oil, sunflower oil, safflower oil, rapeseed oil, maize oil, fish oil, tallow, lard, butterfat, in hydrogenated or non-hydrogenated form, including fractions obtained by dry or wet fractionation and interesterified mixtures obtained from these fats.
  • These fats can be blended in a way known per se to produce suitable margarine fat blends as for instance described in "Margarine", A.J. Ander- sen and Williams, Second Revised Edition, Pergamon Press.
  • the present invention also relates to the production of edible oil- and water-containing emulsions, particularly of the margarine type and of the reduced fat spreads type (containing e.g. 20-60% of fat) where the fat phase contains a fat composition as described above and preferably constitutes the continuous phase of the emulsion.
  • Such emulsions are produced in a way known per se, by emulsifying an aqueous phase with a fatty phase and subjecting an emulsion thus obtained to a texturizing treatment involving cooling and working e.g. in a Votator R equipment or any other equipment well known in the art.
  • the products can also be produced starting from an O/W emulsion which is allowed to invert and give a W/O emulsion.
  • margarines were produced from 84% of a fat composition according to the invention (or alternatively a fat composition used for comparison), 0.16% of lecithin, 0.10% of beta carotene, 0.6% of skim milk, 1% of salt and about 14.14% of water.
  • the margarines were prepared by cooling and plasticizing the above composition using an equipment consisting of 3 scraped-surface heat exchangers (A-units) and 2 crystallizers (C-units) arranged in the following sequence:
  • the margarine samples were stored for 3 days:
  • Fat blends were produced from:
  • the amount of glycerol in (1) was varied from 0.7 to 1.7% to obtain about 16%, 24%, 33% of diglycerides based on the weight of component (1) and 6%, 9%, 12% of diglycerides based on the total fat blend.
  • the corresponding amounts of monoglycerides were 0.6%, 1.0% and 1.2% by weight of the total fat blend.
  • Fat blend A had substantially the same composition as in the parallel examples I - III, except that 0.2% of glycerol was used and that substantially all the mono- and diglycerides were removed by chromatography on a silica column to achieve a level of less than 0.1% of diglyceride and less than 0.05% of monoglyceride in the total fat blend.
  • Fat blend B had substantially the same composition as in the parallel examples I - III, except that 0.2% of glycerol was used, which resulted in the formation of 1.5% of diglycerides and 0.2% of monoglycerides.
  • the texture was assessed using a stainless steel knife with which the products were spread on bread.
  • the oral melt properties were also assessed by measuring the viscosity of the products (after tempering for 30 minutes at 34°C) in a Haake viscosimeter at a shear rate of 100 sec.' 1 .
  • Another method consisted in measuring the salt release temperature i.e. the temperature at which all the salt is released from margarine, which is measured by stirring 1 g margarine with 100 g water which is heated up (1°C/min) from 25°C to 40°C. The salt released is measured conductometrical- ly.
  • Interesterification was carried out with 1% of glycerol as described in Examples I - III. 22% of diglycerides and 2.4% of monoglycerides were formed. Part of the monoglycerides was eliminated by treatment with 20% excess of 1N NaOH, calculated on monoglyceride for 1 hour at 100°C.
  • the interesterified component after the NaOH treatment contained 21% of diglycerides and 0.7% of monoglycerides.
  • Example I The margarine made according to the method described in Example I exhibited a good butterlike texture and a slightly less good melting behaviour than the margarine of Example III.
  • This Example shows that the butterlikeness is less satisfactory when diglycerides having relatively high levels of mono-cis- and di-cis-unsaturated diglycerides are present.
  • a fat composition was produced from:
  • the fat blend contained 11% of diglycerides and about 1.3% of monoglycerides originating from sunflower oil.
  • the margarine exhibited butterlike texture properties that were less pronounced than those of Examples I - IV (panel score on texture: 3; after alternating storage at 5°C and 20°C: 4).
  • the fat solids profile of the fat blend was as follows:
  • the fat blend contained 13% of diglycerides and 1.5% of monoglycerides.
  • the fat solids profile of the fat blend was:
  • the final fat blend contained 14% of diglycerides and 0.9% of monoglycerides.
  • the margarines exhibited very good butter- like properties (panel score: 7.0 after storage at 5°C, 7.0 after storage at alternating temperatures (5°C and 20°C).
  • the fat solids profile was:
  • the salt release temperature was 33°C (which is significantly below body temperature).
  • Example XI The butterlike texture and melting properties of the modified butter according to Example XI were very similar to those of fresh butter, but the modified butter was much better spreadable, especially below 15°C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Edible Oils And Fats (AREA)
  • Fats And Perfumes (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
EP85201190A 1984-07-17 1985-07-15 Diglyceride enthaltendes Fett Expired EP0171112B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85201190T ATE31599T1 (de) 1984-07-17 1985-07-15 Diglyceride enthaltendes fett.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8418154 1984-07-17
GB848418154A GB8418154D0 (en) 1984-07-17 1984-07-17 Edible fat composition

Publications (2)

Publication Number Publication Date
EP0171112A1 true EP0171112A1 (de) 1986-02-12
EP0171112B1 EP0171112B1 (de) 1988-01-07

Family

ID=10563997

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85201190A Expired EP0171112B1 (de) 1984-07-17 1985-07-15 Diglyceride enthaltendes Fett

Country Status (9)

Country Link
US (1) US4656045A (de)
EP (1) EP0171112B1 (de)
JP (1) JPS6163242A (de)
AT (1) ATE31599T1 (de)
AU (1) AU558168B2 (de)
CA (1) CA1262421A (de)
DE (1) DE3561270D1 (de)
GB (1) GB8418154D0 (de)
ZA (1) ZA855347B (de)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0378893A2 (de) * 1989-01-17 1990-07-25 Kao Corporation Essbare Öl-/Fett-Zusammensetzungen
WO1990009107A1 (en) * 1989-02-10 1990-08-23 Grindsted Products A/S (Danisco A/S) A spreadable water-in-oil emulsion
EP0402090A2 (de) * 1989-06-07 1990-12-12 Kao Corporation Essbare Öl-in-Wasser-Emulsion
EP0417562A1 (de) * 1989-09-01 1991-03-20 Kao Corporation Wasser-in-Öl Emulsion
EP0425958A2 (de) * 1989-10-31 1991-05-08 Kao Corporation Doppeltemulgierte Fett- oder Ölzusammensetzung des Öl-in-Wasser-in-Öl-Typs
EP0426155A2 (de) * 1989-10-31 1991-05-08 Kao Corporation Hartbutterzusammensetzung
WO1995022256A1 (en) * 1994-02-18 1995-08-24 Loders Croklaan B.V. Fat blends, based on diglycerides
WO1995022257A1 (en) * 1994-02-18 1995-08-24 Loders Croklaan B.V. Fat blends containing diglycerides
WO1996032022A1 (en) * 1995-04-13 1996-10-17 Unilever N.V. Edible plastic spread
US6117476A (en) * 1999-01-04 2000-09-12 Shaul Eger Healthy food spreads
WO2001013733A1 (en) * 1999-08-24 2001-03-01 Kao Corporation Fat or oil composition
CN105208872A (zh) * 2013-05-16 2015-12-30 雀巢产品技术援助有限公司 结构改造的油组合物

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NL8601078A (nl) * 1986-04-25 1987-11-16 Unilever Nv Aromacompositie, de toepassing daarvan en de werkwijze voor de bereiding ervan.
JPS63126457A (ja) * 1986-11-17 1988-05-30 Kao Corp 焼菓子用油脂のマイグレ−シヨン抑制剤及びそれを用いる複合焼菓子類の製造法
JP2510651B2 (ja) * 1987-02-02 1996-06-26 花王株式会社 油中水型乳化油脂組成物
JPH0740877B2 (ja) * 1987-08-10 1995-05-10 花王株式会社 食用油組成物
JPH0740873B2 (ja) * 1987-04-27 1995-05-10 花王株式会社 可塑性油中水型乳化油脂組成物
JPH0746968B2 (ja) * 1987-07-16 1995-05-24 花王株式会社 液状油脂組成物
JPH0693997B2 (ja) * 1987-09-04 1994-11-24 花王株式会社 油中水型乳化油脂組成物
JPH0724546B2 (ja) * 1987-11-24 1995-03-22 花王株式会社 油中水型乳化油脂組成物
US4959465A (en) * 1988-02-26 1990-09-25 Nabisco Brands, Inc. Low calorie fat mimetics
US5096720A (en) * 1988-08-31 1992-03-17 National Starch And Chemical Investment Holding Corporation Method for enhancing desirable physical and organoleptic properties of food products
DE69016368T2 (de) * 1989-11-22 1995-06-14 Unilever Nv Dispersion mit zusammenhängender lipider Phase und Verfahren zu ihrer Herstellung.
WO1991009533A1 (en) * 1990-01-04 1991-07-11 The Procter & Gamble Company Low saturate, all-purpose plastic shortening with specially hydrogenated intermediate-melting fat component
US5064670A (en) * 1990-04-06 1991-11-12 The Procter & Gamble Company Low-saturate frying fat and method of frying food
JP2938539B2 (ja) * 1990-09-26 1999-08-23 花王株式会社 チョコレート類
US5476678A (en) * 1993-04-23 1995-12-19 Amway Corporation Composition for and method of producing a fiber fortified chewy or soft-textured confection candy
AU698684B2 (en) * 1994-04-29 1998-11-05 Loders Croklaan B.V. Ice-cream coating fats
US5908655A (en) * 1997-10-21 1999-06-01 Danisco A/S Shortening system, products therewith, and methods for making and using the same
JP3550017B2 (ja) * 1998-03-03 2004-08-04 花王株式会社 油中水型乳化油脂組成物
JP3662445B2 (ja) 1999-06-30 2005-06-22 花王株式会社 油中水型乳化油脂組成物
JP3621610B2 (ja) * 1999-08-30 2005-02-16 花王株式会社 油中水型乳化油脂組成物
JP2001262181A (ja) * 2000-03-23 2001-09-26 Kanegafuchi Chem Ind Co Ltd 可塑性油脂組成物
US20030054509A1 (en) * 2001-04-06 2003-03-20 Archer-Daniels-Midland Company Method for producing fats or oils
JP4181781B2 (ja) * 2001-04-13 2008-11-19 花王株式会社 油脂組成物
JP4995377B2 (ja) * 2001-04-26 2012-08-08 花王株式会社 油脂組成物
JP4060670B2 (ja) * 2001-09-28 2008-03-12 花王株式会社 揚げ物の製造法
JP4157765B2 (ja) * 2002-02-18 2008-10-01 花王株式会社 粉末油脂
AR044623A1 (es) * 2003-06-04 2005-09-21 Danisco Grasa vegetal modificada
JP4098276B2 (ja) * 2003-06-16 2008-06-11 花王株式会社 酸性水中油型乳化組成物
EP1651058A4 (de) 2003-07-16 2007-07-11 Archer Daniels Midland Co Verfahren zur herstellung von fetten oder ölen
US20090220653A1 (en) * 2003-08-21 2009-09-03 Danisco A/S Shortening system
DE102004019472A1 (de) * 2004-04-22 2005-11-17 Bayer Healthcare Ag Phenylacetamide
JP4823558B2 (ja) * 2004-04-28 2011-11-24 花王株式会社 油脂組成物
WO2005104865A1 (ja) * 2004-04-28 2005-11-10 Kao Corporation 油脂組成物
EP1759589B1 (de) * 2004-04-28 2011-10-05 Kao Corporation Fettzusammensetzung
JP4674445B2 (ja) * 2004-05-17 2011-04-20 不二製油株式会社 油中水型乳化組成物
WO2006014322A1 (en) * 2004-07-02 2006-02-09 Cargill, Incorporated Fat products containing little or no trans-fatty acids
TWI363600B (en) * 2004-09-21 2012-05-11 Kao Corp Acidic oil-in-water emulsion composition
JP4664176B2 (ja) * 2005-09-30 2011-04-06 理研ビタミン株式会社 可塑性油脂組成物
US7687096B2 (en) * 2005-12-28 2010-03-30 Caravan Ingredients Inc. Non-hydrogenated vegetable oil based margarine for puff pastry containing an elevated diglyceride emulsifier
US20070148314A1 (en) * 2005-12-28 2007-06-28 Lawrence Skogerson Peanut butter having a non-hydrogenated vegetable oil based high diglyceride emulsifier
US7691428B2 (en) * 2005-12-28 2010-04-06 Caravan Ingredients Inc. Non-hydrogenated vegetable oil based shortening containing an elevated diglyceride emulsifier composition
UA97127C2 (uk) * 2006-12-06 2012-01-10 Бандж Ойлз, Инк. Спосіб безперервної ферментативної обробки композиції, що містить ліпід, та система для його здійснення
JP2011144343A (ja) * 2009-12-15 2011-07-28 Kao Corp 精製油脂の製造方法
CA2843196A1 (en) * 2011-08-03 2013-02-07 University Of Guelph Novel 1,3-diacylglycerol (1,3-dag) for hard fat applications
KR20180103165A (ko) * 2016-02-01 2018-09-18 번지 로더스 크로크란 비.브이. 자가-유화 지방 조성물

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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0378893A2 (de) * 1989-01-17 1990-07-25 Kao Corporation Essbare Öl-/Fett-Zusammensetzungen
EP0378893A3 (de) * 1989-01-17 1991-03-27 Kao Corporation Essbare Öl-/Fett-Zusammensetzungen
EP0525915A1 (de) * 1989-01-17 1993-02-03 Kao Corporation Essbare Öl- bzw. Fettzubereitungen
WO1990009107A1 (en) * 1989-02-10 1990-08-23 Grindsted Products A/S (Danisco A/S) A spreadable water-in-oil emulsion
EP0402090A2 (de) * 1989-06-07 1990-12-12 Kao Corporation Essbare Öl-in-Wasser-Emulsion
EP0402090A3 (de) * 1989-06-07 1991-05-08 Kao Corporation Essbare Öl-in-Wasser-Emulsion
US5160759A (en) * 1989-06-07 1992-11-03 Kao Corporation Edible oil-in-water emulsion
EP0417562A1 (de) * 1989-09-01 1991-03-20 Kao Corporation Wasser-in-Öl Emulsion
EP0425958A2 (de) * 1989-10-31 1991-05-08 Kao Corporation Doppeltemulgierte Fett- oder Ölzusammensetzung des Öl-in-Wasser-in-Öl-Typs
EP0426155A2 (de) * 1989-10-31 1991-05-08 Kao Corporation Hartbutterzusammensetzung
EP0426155A3 (en) * 1989-10-31 1992-05-27 Kao Corporation Hard butter composition
EP0425958A3 (en) * 1989-10-31 1992-09-16 Kao Corporation Oil-in-water-in-oil doubly emulsified fat or oil composition
WO1995022256A1 (en) * 1994-02-18 1995-08-24 Loders Croklaan B.V. Fat blends, based on diglycerides
WO1995022257A1 (en) * 1994-02-18 1995-08-24 Loders Croklaan B.V. Fat blends containing diglycerides
US5879735A (en) * 1994-02-18 1999-03-09 Loders-Croklaan B.V. Fat blends, based on diglycerides
US5912042A (en) * 1994-02-18 1999-06-15 Loders Croklaan B.V. Fat blends containing diglycerides
WO1996032022A1 (en) * 1995-04-13 1996-10-17 Unilever N.V. Edible plastic spread
US6117476A (en) * 1999-01-04 2000-09-12 Shaul Eger Healthy food spreads
WO2001013733A1 (en) * 1999-08-24 2001-03-01 Kao Corporation Fat or oil composition
US6495536B1 (en) 1999-08-24 2002-12-17 Kao Corporation Fat or oil composition
EP1702515A2 (de) * 1999-08-24 2006-09-20 Kao Corporation Fett- oder Ölzusammensetzung
EP1702515A3 (de) * 1999-08-24 2006-11-29 Kao Corporation Fett- oder Ölzusammensetzung
US7514472B2 (en) 1999-08-24 2009-04-07 Kao Corporation Fat or oil composition
CN105208872A (zh) * 2013-05-16 2015-12-30 雀巢产品技术援助有限公司 结构改造的油组合物

Also Published As

Publication number Publication date
DE3561270D1 (en) 1988-02-11
ATE31599T1 (de) 1988-01-15
JPS6163242A (ja) 1986-04-01
JPH0434367B2 (de) 1992-06-05
CA1262421A (en) 1989-10-24
AU558168B2 (en) 1987-01-22
GB8418154D0 (en) 1984-08-22
AU4506085A (en) 1986-01-23
ZA855347B (en) 1987-03-25
US4656045A (en) 1987-04-07
EP0171112B1 (de) 1988-01-07

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